Potassium Carbonate → 8-[(Cyclopropyl-methyl-amino)methyl]-6-ethynyl-2,2,4,4-tetramethyl-chroman

HRID 1765713Notes

Reaction equation

HRID 1765713 reaction equation
[CH:1]1([N:4]([CH2:6][C:7]2[CH:8]=[C:9]([C:21]#[C:22][Si](C)(C)C)[CH:10]=[C:11]3[C:16]=2[O:15][C:14]([CH3:18])([CH3:17])[CH2:13][C:12]3([CH3:20])[CH3:19])[CH3:5])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+]>CO>[CH:1]1([N:4]([CH2:6][C:7]2[CH:8]=[C:9]([C:21]#[CH:22])[CH:10]=[C:11]3[C:16]=2[O:15][C:14]([CH3:17])([CH3:18])[CH2:13][C:12]3([CH3:20])[CH3:19])[CH3:5])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 69074520HCID 69074520, compound2×

Product 1

HCID 211072508-[(Cyclopropyl-methyl-amino)methyl]-6-ethynyl-2,2,4,4-tetramethyl-chromanYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 8-[(cyclopropyl-methyl-amino)-methyl]-2,2,4,4-tetramethyl-6-trimethylsilanylethynyl chroman (Intermediate 10, 0.729 g, 1.97 mmol) in methanol (30 mL) was treated with potassium carbonate (1.4 g, 10.2 mmol) and the resulting reaction mixture was stirred at ambient temperature overnight. The solvent was evaporated in vacuo, the residue was diluted with water and extracted with ethyl acetate. The organic phase dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title compound as a brown oil (0.571 g, 98%).

Workup

  1. customthe resulting reaction mixture
  2. customThe solvent was evaporated in vacuo
  3. additionthe residue was diluted with water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-03f9a8b7544940d3bf666eb753df5639
Source dataset
uspto-grants-2007_06
Patent number
US07226951B2

Reaction notes

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